Imidazole → 4-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

HRID 1670816노트

반응식

HRID 1670816 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.N1C=CN=C1.[CH:27]1([CH:33]([CH2:48][CH2:49]O)[C:34]([NH:36][CH2:37][C:38]2[C:43]([Cl:44])=[CH:42][C:41]([O:45][CH3:46])=[CH:40][C:39]=2[Cl:47])=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[Br:20][CH2:49][CH2:48][CH:33]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[C:34]([NH:36][CH2:37][C:38]1[C:43]([Cl:44])=[CH:42][C:41]([O:45][CH3:46])=[CH:40][C:39]=1[Cl:47])=[O:35]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 673553892-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide

생성물 1

HCID 673563304-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Stir a mixture of triphenylphosphine (3.16 g, 12.06 mmol), bromine (1.91 g, 12.06) and methylene chloride (150 mL) at room temperature for 20 minutes. To the mixture, add a solution of imidazole (0.98 g, 14.48 mmol), 2-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide (4.5 g, 12.06 mmol) in methylene chloride (100 mL). Stir the reaction at room temperature for 3.5 hours. Wash the reaction with HCl (1 N), water and brine. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane to afford 2.5 g. of the title compound. MS (m/z): 436 (M+H)+.

후처리

  1. stirringStir
  2. customthe reaction at room temperature for 3.5 hours
  3. washWash
  4. customthe reaction with HCl (1 N), water and brine
  5. dry with materialAfter drying the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane
  9. customto afford 2.5 g

출처 및 근거

ORD 기록
ord-cddb05a3e0884bed93a66cbb2603130f
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994176B2

반응 노트

불러오는 중…